automattic

I originally drafted this post back in January 2015. Like many of you, I have a ton of posts in drafts that I just never got around to publishing. Having worked at Automattic in the past where we were 100% distributed but with frequent in-person meetups, and an SF office for get togethers — today I often get asked about remote/distributed work and if startups should try it. My short answer is that it depends on the org and stage of the company and that more importantly, it’s a false choice to be 100% distributed or 100% in the office. I’ll explain in more detail below.

I’m a big believer that you need in-person time with colleagues, but certainly, most workers don’t need to be in the office every single hour, every single day. So given the current pandemic forcing many of us to work from home, I went looking for this post. And I feel like post-pandemic this might be the right model. So here goes – my thoughts from over five years ago, with the caveat that things have obviously evolved but most of these ideas I still think are relevant to think about:

January 2015:
Great discussion happening right now about the benefits and downsides to working in an office VS being part of a distributed workforce (aka “remote working”).

I actually see arguments for both camps as being pretty solid and think every company needs to decide for itself what works best. My $.02 is that engineering-centric organizations that are very comfortable with async and text-heavy communication tools, will likely have more immediate success than sales heavy organizations. And ultimately it’s an HR challenge, in that distributed workforces need to employ highly independent, motivated, and entrepreneurial folks who don’t need a ton of guidance, and don’t need to be mentored a ton.

But I’d like to make a suggestion for companies who are thinking about this topic. There is no need to be purely distributed, or purely stuck in one office. Go Hybrid!

By Hybrid I mean the following – assume you’ll be in-person for maybe 3 days a week, and the rest of the time your colleagues will work from wherever. For some that will mean a home office, for others a co-working space or a coffee shop.

Specifically:

Have an office near a big city (and/or a good airport) where people will naturally gravitate to, and you’ll be near your customers and partners.

For large companies, have multiple offices. I don’t see the need for mega campuses. You can do meetups for workers that need to collaborate in-person occasionally.

Stop being so rigid on office culture in terms of when people work. Move to being output driven.

For meertings/video/audio calls and the like – try and keep them between reasonable hours that don’t force early morning or late night commutes. ex: only have meetings between 10am and 3pm.. Consider no meetings on Monday and Friday which are heavy traffic / long commute days, and encourage Mon and Fri to be deep project days, where people can grab 2+ hour long chunks of time to go deep on work. If people only commute 3/week and don’t fight rush our, they may actually get more comfortable living a bit further away in a more affordable housing situation.

Use the best tools that highly distributed teams use — Slack, Skype, etc – even when you are in the office.

Document everything! Every meeting should be summarized (Square has been doing this for years), every discussion, every bit of financial and product metrics should be available to all employees.

Work on a handbook to get new employees ramped up quickly. Automattic did an amazing job with this effort.

Invest in internal tools. You need a team ideally dedicated to making “work from anywhere” efficient. You need a search tool, you need a way to understand the big goals, the OKRs, and so much more. The more you make your resources self-serve, the better you’ll do in not needing to be in the office every single moment and a huge secondary effect of this is making new hires more efficient and have quicker ramp=ups.

The days of an expensive office, in a big city, where your employees struggle to find nearby affordable housing just doesn’t feel that viable long-term. But the idea of only being distributed with no in-person interactions also feels challenging and deprives us of the energy we need to create and be happy & productive.

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In many ways, the number seven holds special value. It’s a lucky number in various cultures, the number of days in a week, plays a role in agriculture and crop rotation, and it’s said that your allergies reset and change after seven years. So changing things up after seven years just feels right.

But as one of my editorial colleague back at TIME would frequently remind the team — stop burying the lead. So I’ll take that advice and jump into the TL;DR: After seven incredible, fun, and rewarding years at Automattic, I’m wrapping up in a couple of weeks, and joining Mike Hirshland at Resolute Ventures as a General Partner. Resolute is focused on early stage seed investing, and already has fantastic companies in the portfolio.

When I joined Automattic back in 2007, we were a handful of folks distributed around the world running WordPress.com and Akismet and contributing everything we did to the WordPress open source project. When we got together in person, we could fit around one table in the old Pier38, which was True Venture’s SF office, and later we got a space of our own at the very same pier.

About a year in I recall that Google and others had estimated that WordPress powered about one percent of the web (which we were ecstatic about!). I remember thinking, here was a company with still a couple of dozen people, having raised just over a million dollars in funding – and what a big impact already!.

Fast forward to today and WordPress is powering over 22% of the web. Automattic is 250 people in 190 cities and 30 countries, profitable (and now with a war chest), a positive force for the open web, and we are still contributing everything we do back into a huge open source project. As Matt Mullenweg, the founder and CEO of Automattic likes to say, “we open source everything but our password files.” It’s a powerful concept, and one that has held true at Automattic for all these years.

Looking at our growth, I decided to flip through the annual company meetup photos over the past few years. It’s fun to look at these photos as a nice visual on just how much the company grew:

2007 company meetup in Stinson Beach

2008 company meetup in Arizona

Late 2008 company meetup in Colorado

2009 company meetup in Canada

2010 company meetup in Florida

2011 company meetup in Budapest

2012 company meetup in San Diego

2013 company meetup in Santa Cruz

I want to especially thank Matt Mullenweg and Toni Schneider for making this an amazing journey. We sketched out some big ambitious plans (often at Crossroads) all those years ago, and it’s incredible to look at where things are now and see how many of those big ideas became a reality. When we started talking about my transition a while back, Matt & Toni were super supportive and it was fun (and a bit nostalgic) to walk down memory lane and add up all the amazing experiences we’ve had together.

I loved every second at Automattic, and have learned a ton along the way. I loved the way we worked and focused on output, and put engineers at the center of the company. Automattic and WordPress will always be part of my DNA, and I can’t wait to see what the talented team tackles next. In fact, I’ll remain an advisor to Automattic, and you’ll still see me out there championing the cause of democratizing publishing. For anyone looking to work at a fast paced, fun, and big impact type of organization – I can 100% recommend working at Automattic.

I also want to thank Phil Black, Jon Callaghan, Tony Conrad, and the whole team at True Ventures. I’ve known many of them even longer than my colleagues at Automattic, and they are just a tremendous group of people who are the embodiment of integrity and loyalty. I’ve learned so much from them, and in many ways they provided the spark that got me hooked on working with early stage companies.

In terms of Resolute Ventures – this was an opportunity that was tailor made for me. My passion is working right in the intersection of technology and entrepreneurship. I’ve always been both a tech entrepreneur who is passionate about building businesses and working on product, and a business guy who thinks the more technical you are, the closer you are to the truth.

I love working with founders and helping early stage companies navigate and make sense of the amazing opportunities and the chaos. I’ve founded companies back in the web 1.0 days, worked at large media companies in NY, and have helped grow Automattic the last few years wearing many different hats — from building up our enterprise VIP business to most recently heading up corp dev and partnerships. The highlights for me at Automattic were definitely helping bring people on board either through hiring or acquisitions — and seeing fantastic people make great contributions has been incredibly rewarding.

Mike Hirshland, the founder of Resolute Ventures, is someone well known here in the Valley, especially for a guy based in Boston. I’ve known him for close to a decade, and he served on our board at Automattic for many years while at Polaris and was part of the original investors in Automattic. Many of you know him from Dogpatch Labs, which he ran, and where Instagram and many other companies got their start. He’s a true advocate for founders, and blends hard work, persistence, and self deprecating humor into something magical.

Part of me is definitely a bit sad to be leaving my family at Automattic, but I’m excited for the next chapter and can’t wait to work with all the fantastic people who are part of Resolute. A special shout-out to my friends who helped me with this transition and were so generous with their time and insights.

So here goes something new — and I’m looking forward to the next seven years and beyond.

I’ll start with the big stuff: Automattic is raising $160M, all primary, and it’s the first investment into the company since 2008. This is obviously a lot of money, especially considering everything we’ve done so far has been built on only about $12M of outside capital over the past 8 years.

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Scott Berkun, a former colleague of mine, has published a very interesting book about his time at Automattic / WordPress.com – and how we work in our flat and distributed way.

The book is called The Year Without Pants (an inside joke related to being able to work from anywhere in the world, including from home ), and is focused on Scott’s time at Automattic, and what it’s like to work at a company, that among other things, has no central office and doesn’t use email internally.

As Eric Ries mentions:

“Most talk of the future of work is just speculation, but Berkun has actually worked there. The Year Without Pants is a brilliant, honest, and funny insider’s story of life at a great company.” —Eric Ries, author, New York Times bestseller The Lean Startup

Scott has a few bits about yours truly, and my sleep deprived startup life:

The first striking thing about Raanan was that he never seemed to sleep. I didn’t understand if there were two or more of him who worked in shifts or if his genetics allowed him to work at twice normal speed, but he seemed to know what was going on everywhere, all the time … Raanan loved what he was doing. He’d joined in part because of the mission to democratize publishing.

A bit surreal to read about your own work, and I’ve found over the years that all my colleagues have a great work ethic.

What I like is that Scott hits on a point that I find very true — which is that companies that have big audacious goals such as ours, and give employees freedom to define the methods of achieving them – tend to attract people who are passionate and love what they do. And that combo tends to result in amazing outcomes and companies that have a culture that attracts fantastic talent.

Tiger Global has recently invested over $50M in Automattic secondary stock purchases. After many years of being backed by a great team of investors who have been with Automattic since the early days – Polaris Partners, True Ventures, Radar Partners, and the New York Times Company – Tiger has joined this illustrious group by purchasing shares from early Automattic investors and employees. Along with the on-going growth of WordPress (now powering over 18% of sites on the internet) and the amazing Automattic team (now over 170 employees), this investment is another milestone in our journey towards building a great company.

It’s noteworthy that Tiger has recently invested in companies like SurveyMonkey and Eventbrite, and before that companies like LinkedIn and Facebook. Those names provide a sense of how far Automattic has come and how we’re poised to enter an exclusive circle of successful software companies that are built to last.

Anyway, wanted to get in front of the news that will inevitably come out in the next week or two: there has been a large secondary transaction in Automattic stock, about $50M worth. “Secondary” means that it’s existing stockholders, like the earliest investors or employees, selling stock to another investor versus money going into the company (“primary”). It was led by Lee Fixel at Tiger Global, one of the behind-the-scenes quiet geniuses that has previously invested in SurveyMonkey, Facebook, LinkedIn, Palantir, Square, Warby Parker… Automattic is healthy, generating cash, and already growing as fast as it can so there’s no need for the company to raise money directly — we’re not capital constrained.

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I gave a talk at USC earlier this week about Automattic and WordPress — something I’ve done for 3 years in a row now.

It’s always a ton of fun, and I make sure to do a survey (by show of hands) each time to see what these undergrad & grad students are using in terms of popular services.

Here are the results:
– WordPress: about 75%+ use WordPress in some capacity
– Facebook: 100%
– Twitter: about 75%
– Tumblr: 33%
– Note taking: Evernote vs Simplenote vs Pen & Paper: About 33% Evernote, the rest a combination of email, other apps, or nothing. And one person still using a pen & paper.
– iOS vs Android: 75% iOS, 25% Android
– SMS vs GroupMe vs MessageMe vs Snapchat: SMS still used by everyone, but the surprise here was Snapchat being used by over 50% of the class.

I asked the obvious question of what they were using Snapchat for – and the answer was that it was just a free SMS-like service, easy to send media, works all over the world and w/ friends overseas — and basically that everyone is on it. Was pretty clear it’s moved beyond the salacious roots (or at least how it was covered early on).

So a big thanks to Zach Posner for having me, and for his entire class for engaging in a really fun and interesting discussion – appreciate the tweets and Instagrams too 🙂

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We (Automattic) hosted an event today with Mayor Gavin Newsom for the beta launch of DataSF.org.

Really smart initiative around providing public data to the citizens of San Francisco:

The new web site will provide a clearinghouse of structured, raw and machine-readable government data to the public in an easily downloadable format. For example, there will be updated crime incident data from the police department and restaurant inspection data from the Department of Public Health. The initial phase of the web site includes more than 100 datasets, from a range of city departments, including Police, Public Works, and the Municipal Transportation Agency

I travel a lot, but when I’m in San Francisco, I usually work from home. Everyone else works from home, too. We’re a virtual company. We recently got an office on Pier 38, a five-minute walk from my apartment. I’ll go to there once a week, usually Thursdays, and for board meetings, which happen about once every two months. We leased it so we wouldn’t have to keep borrowing conference rooms from our VC partners. It’s kind of sad; we have this great space right on the water — and six days a week, it’s empty. Of the 40 people working for the company, eight are in the Bay Area, but that’s just a coincidence. They could be anywhere in the world.

We all communicate using P2, something we launched that allows users to publish group blogs in WordPress. It’s a bit like Twitter, but the updates come in real time. With P2, we can share code and ideas instantly. There is a dedicated channel for each part of the company, and when there’s a new message, it shows up in red. It may be someone talking about development or what he or she had for breakfast. I also use Skype for one-on-one and mini group chats.

In my home office, I have two large, 30-inch computer monitors — a Mac and a PC. They share the same mouse and keyboard, so I can type or copy and paste between them. I’ll typically do Web stuff on the Mac and e-mail and chat stuff on the PC. I also have a laptop, which I have with me all the time, whether I’m going overseas or to the doctor’s office. I’m pretty rough on my laptops. I go through about two a year. I keep a server for my home network in the closet. I really enjoy computer networking. I sometimes do tech support for our employees who live in the Bay Area.

I know people I talk to are always fascinated by our organization and how we are setup and completely virtual. This piece provides a few more good insights as to how it all works.